1-octadecyl-2,3,3-trimethylindoleninium iodide | 73811-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-octadecyl-2,3,3-trimethylindoleninium iodide
• 英文别名: 3H-Indolium, 2,3,3-trimethyl-1-octadecyl-, iodide；2,3,3-trimethyl-1-octadecylindol-1-ium;iodide
• CAS: 73811-00-4
• 化学式: C₂₉H₅₀N*I
• 分子量: 539.627
• InChiKey: KQZMCGJLGPJJHX-UHFFFAOYSA-M

物化性质

• 熔点：
  85-88 °C

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-octadecyl-2,3,3-trimethylindoleninium iodide 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 6.67h， 生成 8-bromo-3',3'-dimethyl-6-nitro-1'-octadecyl-1',3'-dihydro-spiro[chromene-2,2'-indole]
  参考文献：
  名称：

  1-octadecyl- and 3,3-diphenyl-substituted photochromic indolinospirochromenes

  摘要：

  DOI：

  10.1007/bf00475389
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 、 1-碘十八烷 生成 1-octadecyl-2,3,3-trimethylindoleninium iodide
  参考文献：
  名称：

  Synthesis and Metastable Structure of New Photochromic Spiroindolinobenzothiopyrans

  摘要：

  我们制备出了具有甲基丙烯酰氧基甲基的光致变色螺吲哚啉基苯并噻喃，并根据光谱数据证明其彩色形式是一种齐聚物结构。

  DOI：

  10.1246/cl.1991.209

文献信息

• [EN] LIPID DERIVATIVES FOR IN VITRO OR IN VIVO DELIVERY<br/>[FR] DÉRIVÉS LIPIDIQUES POUR ADMINISTRATION IN VITRO OU IN VIVO
  申请人：UNIV COLORADO REGENTS

  公开号：WO2019126565A1

  公开（公告）日：2019-06-27

  The present invention relates to novel constructs that allow for delivery of biologically active agents into cells. In certain embodiments, the constructs comprises conjugates of a lipophilic membrane dye, or a derivative or analogue thereof, with the biologically active agent.

  本发明涉及允许将生物活性剂递送入细胞的新颖构建体。在某些实施例中，构建体包括脂溶性膜染料或其衍生物或类似物的偶联物与生物活性剂的结合。
• Survey, fluorescence spectra, and solubility of liquid cyanine dyes
  作者：Masaki Matsui、Takaya Yamamoto、Yasuhiro Kubota、Kazumasa Funabiki

  DOI：10.1039/c6nj02160c

  日期：——

  synthesized four liquid cyanine dyes, namely N,N′-didodecyl 44,N,N′-dioctadecyl indolenium 45,N,N′-bis(2,5,8-trioxa-10-octadecanyl)benzoxazolium 50 and benzothiazolium 51, which have a bis(perfluorobutylsulfonyl)imide anion. In the neat form, these liquid dyes exhibit more intense fluorescence at −196 °C than at 25 °C. The liquid N,N′-dialkylated indolenium derivatives 44 and 45 exhibited larger solubility

  我们合成了四种液体花青染料，分别是N，N'-二十二烷基44，N，N'-二十八烷基吲哚45，N，N'-双（2,5,8-三恶唑-10-十八烷基）苯并恶唑50和苯并噻唑鎓51，其具有双（全氟丁基磺酰基）酰亚胺阴离子。以纯净的形式，这些液体染料在-196°C处比在25°C下表现出更强的荧光。液态的N，N'-二烷基化的吲哚衍生物44和45在己烷中的溶解度大于相应的固态衍生物。另外，液态氮，N′-双（2,5,8-三氧杂-10-十八烷基）苯并恶唑鎓和苯并噻唑鎓衍生物50和51比相应的固体衍生物更易溶于丙醇。
• Synthesis and Metastable Structure of New Photochromic Spiroindolinobenzothiopyrans
  作者：Masafumi Hirano、Akira Miyashita、Hiroyuki Nohira

  DOI：10.1246/cl.1991.209

  日期：1991.2

  Photochromic spiroindolinobenzothiopyrans having a methacryloxymethyl group have been prepared and their colored forms were demonstrated to be a zwitterionic structure on the basis of the spectroscopic data.

  我们制备出了具有甲基丙烯酰氧基甲基的光致变色螺吲哚啉基苯并噻喃，并根据光谱数据证明其彩色形式是一种齐聚物结构。
• Negative Photochromism of a Spiropyran in a Langmuir–Blodgett Film
  作者：Yasushi Yokoyama、Wakana Hara、Tsuguya Inoue、Takashi Ubukata、Masaru Sakomura、Hideyuki Tukada

  DOI：10.1246/cl.2005.1622

  日期：2005.12

  An indolinospiropyran possessing one long alkyl chain on the nitrogen atom of the indoline moiety and two nitro groups on the benzopyran ring, exhibiting negative photochromism in various organic solvents, showed negative photochromism in a Langmuir–Blodgett film. The change in the surface appearance was observed by atomic force microscopy after the visible light irradiation.

  一种在吲哚啉分子的氮原子上有一条长烷基链、在苯并吡喃环上有两个硝基的吲哚啉螺吡喃，在各种有机溶剂中表现出负光色性，在朗缪尔-布洛杰特薄膜中也表现出负光色性。通过原子力显微镜观察到了可见光照射后表面外观的变化。
• Pyrene-fused dioxaborine-based merocyanines with high brightness, photostability, and fluorogenic function for deep-skin tissue imaging of a living mouse
  作者：Haruka Nishihara、Mai Watanabe、Ryosuke Kawakami、Masamoto Murakami、Hitomi Seki、Katsuki Osaki、Teruko Tsuda、Takeshi Imamura、Shingo Hadano、Shigeru Watanabe、Yosuke Niko

  DOI：10.1093/bulcsj/uoad027

  日期：2024.3.1

  Bright polymethine dyes, typified by carbocyanines, are employed in various fluorescence techniques such as the 3D visualization of living cell morphology and the tracking of extracellular vesicles in the blood vessels of a zebrafish. However, they often exhibit low photostability, particularly for dyes with red-shifted absorption/fluorescence wavelengths due to extended polymethine length, and limited photofunctionality. This limitation restricts their utility in specific applications requiring high-power excitation and/or a wash-free approaches. This study introduces novel merocyanine dyes, MCPY3 and MCPY5, comprising a newly developed pyrene-fused dioxaborine and polymethine chain. Despite their minimal polymethine lengths, their absorption/fluorescence wavelengths reside in the red to near infra-red regions due to the substantial π-conjugation system of pyrene. Moreover, they exhibit a considerably superior photostability to carbocyanine dyes and fluorogenic behavior between low (ON) and high (OFF) polar solvents, while maintaining brightness comparable to carbocyanine. Leveraging these advantages, the hydrophilic analogs of MCPY3, MCPY3S, were applied to two-photon microscopy imaging of the skin tissues on the finger of a living mouse. The dye clearly visualized the individual cell morphology in the epidermis and the elastin within the dermis, highlighting the potential of the new dye as a valuable tool for fundamental dermatological and histological studies.

  摘要 以羰花青为典型代表的明亮聚甲基染料被用于各种荧光技术中，如活细胞形态的三维可视化和斑马鱼血管中细胞外囊泡的追踪。然而，它们通常表现出较低的光稳定性，特别是对于由于延长了聚甲基长度而导致吸收/荧光波长红移的染料，以及有限的光功能性。这种局限性限制了它们在需要高功率激发和/或免清洗方法的特定应用中的实用性。本研究介绍了新型美罗菁染料 MCPY3 和 MCPY5，它们由新开发的芘融合二氧硼烷和聚甲基链组成。尽管它们的聚甲基长度极小，但由于芘的大量π-共轭体系，它们的吸收/荧光波长位于红至近红外区域。此外，它们的光稳定性大大优于碳菁染料，在低极性溶剂（开）和高极性溶剂（关）之间都具有荧光特性，同时还能保持与碳菁染料相当的亮度。利用这些优势，MCPY3 的亲水性类似物 MCPY3S 被应用于活体小鼠手指皮肤组织的双光子显微成像。这种染料能清楚地观察到表皮中的单个细胞形态和真皮中的弹性蛋白，突出了这种新型染料作为皮肤病学和组织学基础研究的重要工具的潜力。